How does KAYAK find such low prices on flights from Hawaii to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Hawaii to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$212 CHEAP FLIGHTS from Hawaii to Chicago

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Cheap Flights from Hawaii to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Hawaii to Chicago

Thu, Sep 24 - Wed, Sep 30

9:54 pm - 6:01 pmLIH Lihue-ORD Chicago O'Hare Intl

15h 07m1 stop Seattle/Tacoma Intl

12:50 pm - 7:10 pmORD Chicago O'Hare Intl-LIH Lihue

11h 20m1 stop Seattle/Tacoma Intl

$424Delta

Wed, Sep 23 - Wed, Sep 30

9:54 pm - 1:29 pmLIH Lihue-ORD Chicago O'Hare Intl

10h 35m1 stop Seattle/Tacoma Intl

12:50 pm - 7:10 pmORD Chicago O'Hare Intl-LIH Lihue

11h 20m1 stop Seattle/Tacoma Intl

$424Delta

Thu, Nov 5 - Sun, Nov 8

3:15 pm - 11:35 amHNL Honolulu-MDW Chicago Midway

16h 20m1 stop Oakland

10:15 am - 9:05 pmMDW Chicago Midway-HNL Honolulu

14h 50m1 stop Sacramento Intl

$434Southwest

Wed, Oct 28 - Sun, Nov 1

8:15 am - 5:00 amHNL Honolulu-MDW Chicago Midway

15h 45m1 stop San Jose

10:10 am - 9:10 pmMDW Chicago Midway-HNL Honolulu

15h 00m1 stop San Jose

$434Southwest

Thu, Sep 17 - Mon, Sep 21

10:40 pm - 7:21 pmOGG Kahului-ORD Chicago O'Hare Intl

15h 41m1 stop San Diego

7:20 am - 9:37 pmORD Chicago O'Hare Intl-OGG Kahului

19h 17m1 stop San Diego

$434Alaska Airlines

Tue, Jan 26 - Tue, Feb 2

8:30 pm - 11:09 amLIH Lihue-ORD Chicago O'Hare Intl

10h 39m1 stop Denver Intl

7:15 am - 5:08 pmORD Chicago O'Hare Intl-LIH Lihue

13h 53m1 stop Denver Intl

$438United Airlines

Tue, Oct 20 - Wed, Oct 28

7:00 am - 5:40 amOGG Kahului-ORD Chicago O'Hare Intl

17h 40m1 stop Seattle/Tacoma Intl

2:21 pm - 9:59 pmORD Chicago O'Hare Intl-OGG Kahului

12h 38m1 stop San Diego

$449Alaska Airlines

Tue, Jan 26 - Tue, Feb 2

11:06 am - 1:13 pmLIH Lihue-ORD Chicago O'Hare Intl

22h 07m2 stops Honolulu Portland

2:13 pm - 6:42 amORD Chicago O'Hare Intl-LIH Lihue

20h 29m2 stops San Diego Honolulu

$462Multiple Airlines

Fri, Oct 16 - Wed, Oct 21

10:36 am - 1:25 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 49m1 stop San Diego

2:21 pm - 11:10 amORD Chicago O'Hare Intl-KOA Kona Intl

25h 49m2 stops San Diego Kahului

$470Multiple Airlines

Wed, Sep 9 - Sun, Sep 13

1:03 pm - 4:45 amLIH Lihue-ORD Chicago O'Hare Intl

10h 42m1 stop Los Angeles

5:00 am - 11:59 amORD Chicago O'Hare Intl-LIH Lihue

11h 59m1 stop San Francisco

$552United Airlines

Recent last minute flight deals from Hawaii to Chicago

Wed, Aug 26 - Sun, Aug 30

9:55 pm - 5:00 pmLIH Lihue-ORD Chicago O'Hare Intl

14h 05m1 stop Seattle/Tacoma Intl

6:00 am - 7:16 pmORD Chicago O'Hare Intl-LIH Lihue

18h 16m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$490Delta

Wed, Aug 26 - Sun, Aug 30

9:55 pm - 8:30 pmLIH Lihue-ORD Chicago O'Hare Intl

17h 35m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County

6:00 am - 7:16 pmORD Chicago O'Hare Intl-LIH Lihue

18h 16m2 stops Minneapolis St Paul Seattle/Tacoma Intl

$495Delta

Wed, Aug 26 - Sun, Aug 30

10:00 pm - 2:54 pmLIH Lihue-ORD Chicago O'Hare Intl

11h 54m1 stop Los Angeles

7:00 am - 8:09 pmORD Chicago O'Hare Intl-LIH Lihue

18h 09m1 stop Los Angeles

$542American Airlines

Wed, Aug 26 - Tue, Sep 15

12:45 pm - 6:20 amHNL Honolulu-ORD Chicago O'Hare Intl

12h 35m1 stop Seattle/Tacoma Intl

6:00 am - 9:08 pmORD Chicago O'Hare Intl-HNL Honolulu

20h 08m2 stops Seattle/Tacoma Intl Los Angeles

$629Multiple Airlines

Fri, Aug 28 - Tue, Sep 29

12:30 pm - 1:22 pmHNL Honolulu-ORD Chicago O'Hare Intl

19h 52m1 stop San Diego

7:20 am - 8:26 pmORD Chicago O'Hare Intl-HNL Honolulu

18h 06m1 stop San Diego

$648Multiple Airlines

Sun, Aug 30 - Fri, Sep 11

9:45 pm - 4:05 pmKOA Kona Intl-ORD Chicago O'Hare Intl

13h 20m1 stop Phoenix Sky Harbor Intl

6:55 am - 4:00 pmORD Chicago O'Hare Intl-KOA Kona Intl

14h 05m1 stop Los Angeles

$650American Airlines

Wed, Aug 26 - Sun, Aug 30

8:25 pm - 4:10 pmLIH Lihue-MDW Chicago Midway

14h 45m2 stops Las Vegas Harry Reid Intl Denver Intl

6:10 am - 2:15 pmMDW Chicago Midway-LIH Lihue

13h 05m2 stops San Diego Honolulu

$705Southwest

Wed, Aug 26 - Sun, Aug 30

8:25 pm - 4:10 pmLIH Lihue-MDW Chicago Midway

14h 45m2 stops Las Vegas Harry Reid Intl Denver Intl

5:25 am - 12:35 pmMDW Chicago Midway-LIH Lihue

12h 10m1 stop Las Vegas Harry Reid Intl

$720Southwest

Thu, Aug 27 - Mon, Aug 31

12:04 pm - 5:59 amKOA Kona Intl-ORD Chicago O'Hare Intl

12h 55m1 stop San Francisco

7:50 pm - 12:48 pmORD Chicago O'Hare Intl-KOA Kona Intl

21h 58m2 stops Dallas/Fort Worth San Francisco

$851United Airlines

Wed, Aug 26 - Wed, Sep 2

7:00 am - 11:59 pmHNL Honolulu-ORD Chicago O'Hare Intl

11h 59m2 stops Los Angeles Denver Intl

5:00 am - 1:26 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 26m2 stops Denver Intl San Francisco

$1,061United Airlines

Useful Info

Low season	January
High season	December

Best time to beat the crowds with an average 31% drop in price.

Most popular time to fly and prices are also 3% lower on average.

How does KAYAK find such low prices on flights from Hawaii to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Hawaii to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Hawaii

First Class flights to Chicagofrom $6,906

Business Class flights to Chicagofrom $3,490

Premium Economy Class flights to Chicagofrom $2,211

Economy Class flights to Chicagofrom $477

$212 Find Cheap Flights from Hawaii to Chicago - Compare and Save

Cheap Flights from Hawaii to Chicago

Recent round-trip flight deals from Hawaii to Chicago

Recent one-way flight deals from Hawaii to Chicago

Recent last minute flight deals from Hawaii to Chicago

Recent direct flight deals from Hawaii to Chicago

Good to know

Low season

High season

FAQs for booking flights from Hawaii to Chicago

Traveling to a place near Chicago?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Hawaii

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight